I use Jake's method of the winch. I have a nice stainless ring that is attached near the top of my mast support. The line from the winch goes through that before I attach it to the forestay (trap wire okay too). This way the line can pull as much up as possible. The boat is usually still tied to the trailer so it will not pull forward. By te way I also loosen one side of the shrouds so the rig will be easy to put all the pins in. My crew Eileen (125lbs) holds the top part of the mast while I set the base in. I do not use the pin or anything to keep the mast in. I crank on the winch until the mast is light in her hands when it is over her head, this keeps the mast in. Then when I get on the boat to guide the mast up I do not have too much weight to hold (it is preloaded) while she goes to the front and cranks the winch. I do not have to muscle the mast at all this way. When the mast is straight up there is nothing to much to hold. She then can take the winch line off and attach the bridle wire. We tighten the shroud after the mast is up.

The mast is not as heavy as a 20, the boat we had before, but I still use the same method...I like it.

Later,
Dan